JPS6239661A - Monoazo dye - Google Patents

Abstract

NEW MATERIAL:The compound of formula I (X is halogen, 1-8C alkoxy, trifluoromethyl, 1-8C alkylsulfonyl, formyl, etc.; Y is H, Cl, methyl, 1-8C alkoxy or acylamin; R<1> is H, alkenyl, aryl, 1-8C alkyl or substituted 1-8C alkyl). EXAMPLE:The compound of formula II. USE:A dye for dyeing a synthetic fiber or cloth, etc., such as polyester fiber, etc., in orange - blue color. It has excellent moisture fastness after post- treatment. PREPARATION:The amine of formula III is diazotized and coupled with the compound of formula IV.

Description

DETAILED DESCRIPTION OF THE INVENTION (Industrial Application Field) The present invention relates to monoazo dyes.
For example, it relates to a monoazo dye that can dye synthetic fibers such as polyester rutted fibers or cloth produced therefrom orange to blue.

(Prior art) As a dye for dyeing synthetic fibers such as polyester fibers, it has excellent light fastness, sublimation fastness, and wet fastness, as well as excellent dyeing physical properties such as fan dependence during dyeing. Various dyes have been proposed and put into practical use by comprehensively considering these physical properties.

On the other hand, in recent years, the surface of polyester cloth is often subjected to processing treatments (hereinafter referred to as post-processing treatments) for the purpose of, for example, water repellency, improving texture, antistatic properties, or antibacterial properties. This post-processing treatment usually involves applying an organic agent such as polyurethane or silicone to the surface of the polyester fabric.
This is carried out by heat treatment at a high temperature of 0 to 8 degrees Celsius/gO'C, but in this case there is a drawback that the dye that has already been dyed on the cloth bleeds out. Therefore, in general, there is almost no improvement in light fastness and sublimation fastness of dyed fabrics after post-processing, but in particular, wet fastness tends to be significantly lower compared to post-processing. There is.

For example, Tokko Sho Q! The monoazo dye shown by the structural formula below, which is specifically disclosed in Publication No. 77/2, has a vivid color tone similar to that of anthraquinone dyes, and has good fastness to light, sublimation fastness, and wet fastness. It is also a very good dye. However, after the above-mentioned post-processing, the wet fastness such as washing fastness, alkali sweat fastness, water fastness, etc. becomes extremely low, which poses a problem as a dye for post-processing.

(Problems to be Solved by the Invention) The present invention provides a monoazo dye that has good wet fastness after post-processing without impairing its physical properties such as bright color tone and excellent light fastness and sublimation fastness. It is intended for the purpose of providing.

(Means for solving intervening vertices) That is, the gist of the present invention is the following general formula CI) (wherein,
X is a halogen atom, C1-C8 alkoxy group, trifluoromethyl group, C1-C, alkylsulfonyl group, formyl'&sc+-c8 alkylcarbonyl x, C1-C
δ represents an alkoxycarbonyl group, an aryloxyalkoxycarbonyl group, or an aralkyloxycarbonyl group, and Y is a hydrogen atom, a chlorine atom, a methyl group, 01 to c8
Represents an alkoxy group or an acylamino group, and R' is hydrogen W-1--rrunyl accent? II n list r+, ts
-rn, Kyl group or C1-C8 alkoxy group, cyano group, chlorine atom, acyloxy group, C8-C6 alkoxyalkyl group, phenyl group, phenyloxy group, aralkyloxy group, carbamoyl group, N-alkyl- Aminocarbonyl group, C1-C, alkoxycarbonyl group, phenoxyalkoxycarbonyl group, aralkyloxycarbonyl A4, C1-C8 alkoxycarbonyloxy group, benzyloxycarbonyloxy group, phenyloxycarbonyloxy group, succinimide group, phthalic acid The gist thereof is a monoazo dye represented by C1-C, which represents an alkyl group which may be substituted with an imide group or a cyanoalkoxy group.

Among the dyes represented by the forefoot general formula [I] of the present invention, particularly preferred dyes are those in which X is a chlorine atom or a bromine atom, Y is a methyl group or an acetylamino group, and F is a C
1-C8 alkyl group, c.

~C8 alkoxyalkyl group, cyanoethylchloroethyl group, phenoxyethyl group, acyloxydiethyl group, phenylC0-C, alkyl group, carbamoylethyl group,
Examples include an N-alkyl-aminocarbonylethyl group or a succinimidoethyl group.

In the present invention, only the dye obtained by combining the specific diazo component and the specific coupling component described above shows good wet fastness after post-processing.

The monoazo dye represented by the general formula [1] is usually obtained by diazotizing the amine represented by the following formula [113 (in the formula or the same as the above definition) by a conventional method, and then by diazotizing the amine represented by the following formula [113 (in the formula or the same as the above definition)]. C. Polyethylene terephthalate, terephthal P and t,y-bis-
Polyester fibers such as polycondensates (such as polycondensates with (hydroxymethyl)cyclohexane), or blends and mixed products of natural fibers such as cotton, silk, and annual wool with the above polyester fibers are excluded.

In order to dye polyester fibers using the dye of the present invention, since the dye represented by the general formula [I] is insoluble or dissolvable in water, naphthalene sulfonic acid and formaldehyde are used as dispersants in a conventional manner. Dyeing or printing may be carried out by preparing a dyeing bath or printing using all condensates, higher alcohol sulfuric esters, higher alkylbenzene sulfonates, etc. and dispersing them in an aqueous medium. For example, in the case of dip dyeing, polyester fibers or their blends can be dyed with excellent fastness by applying ordinary dyeing methods such as high temperature dyeing, carrier dyeing, and thermosol dyeing. 9. Optionally, even better results can be obtained by adding acidic substances such as formic acid, acetic acid, phosphoric acid or ammonium sulfate to the dyeing bath.

Furthermore, the monoazo dye of the present invention represented by the general formula [■] for the front paw may be used in combination with dyes of the same type or dyes of other systems, and among these, the monoazo dye of the present invention represented by the general formula [I] for the paw In some cases, good results such as improved dyeability can be obtained by blending.

(Examples) Next, the present invention will be explained in more detail with reference to Examples, but the present invention is not limited to the following Examples.

Example 1 Monoazo dye represented by the following structural formula 0. ! ;? was dispersed in 3 t of water containing naphthalene sulfonic acid-formaldehyde condensate TG- and higher alcohol sulfate ester COP to prepare a dyeing bath. Polyester fiber ioog in this dyeing bath
- was immersed and dyed at 130°C for 60 minutes, followed by soaping, watering, and drying. As a result, a clear W-like red dyed fabric was obtained. The light fastness, sublimation fastness and water fastness of the obtained dyed fabric, as well as the temperature stability and pH stability during dyeing of the above dye were good.

Next, the obtained dyed fabric was further subjected to polyurethane processing (wind processing), and the wet fastness after processing (washing fastness, alkali sweat fastness, and water fastness) was determined according to the following method, and the results are shown below. It is shown in Table 1.

(1,1 polyurethane processed Vidran p-xlIK (manufactured by Dainippon Ink Co., Ltd.,
After soaking in a 7% solution of (trade name), cure for one minute with tAOC.

(2) Washing Ifi 1 fastness: Attach multi-fiber to a dyed cloth treated with polyurethane and perform a washing test according to AATCC Law Laundry No. 118 to reduce the contamination of the nylon fibers of the multi-fiber to gray scale. It was determined that

(3) Alkaline sweat fastness JIS I dyed cloth with polyurethane treatment.

The test was conducted according to the -θg'IgA method, except that nylon cloth and silk cloth were used as the attached cloths, and the degree of contamination of the silk cloths was determined on a gray scale.

(4) Water fastness JIS L-Or' dyed fabric treated with polyurethane
The test was conducted in accordance with the IAA method, except that silk cloth was attached instead of nylon cloth, and the degree of contamination of the silk cloth was determined on a gray scale.

The dye used in this example was produced as follows.

11 Amino Danitro 6-chlorobenzothiazole LA? is dissolved in phosphoric acid l- and acetic acid tS-, -3
Diazotization was carried out using guyutinitrosyl sulfuric acid at ℃, and the resulting diazo liquid was added to 300 ml of total j% sulfuric acid /-N-acetoxy x f /l/ -2,2゜da, kutetramethyl-/
,:l,J,'l-tetrahydroquinoline! , was added dropwise to a solution containing 5 g of the solution at a temperature of 8 to s°C. The precipitated crystals were filtered and dried to obtain reddish-brown crystals (yield: gq%).

Also, the λmax (acetone) of this product is! ; , r l
r nm.

Example: A dye represented by the following structural formula: 0. , lr f as naphthalene sulfonic acid-formaldehyde condensate O3! ? was mixed with paint and pulverized with Paint 7 Acre to obtain a finely divided dye. Colored paste 1007 was obtained by thoroughly mixing with the base paste having the composition shown below.

Composition of original paste Carboxymethyl cellulose glue 3 o y.

Tartaric acid o, ay-aromatic carrier 0.31 (Sunfloren SN
, manufactured by NICCA CHEMICAL INDUSTRY CO., LTD., product name) Total? 9.09 - This colored paste was printed on polyester fibers, intermediately dried at 100°C, and then kept in superheated steam at 170°C for 7 minutes to develop color, followed by annealing, washing with water, and drying. As a result, a polyester cloth printed in red with good light fastness, sublimation fastness, and wet fastness was obtained.

Next, the obtained dyed fabric was processed with polyurethane, and the wet fastness after processing was measured in the same manner as in Example 1, and the results are shown in Table 1 below.

Note that the dye used in this example was manufactured according to the method described in Example/. Moreover, λm&X (acetone) of this product was j 4' 4 nm.

Comparative Examples 1 to 3 Polyester cloth was dyed using the dyes shown in Table 1 below, and the resulting dyed cloth was subjected to polyurethane processing, and then the wet fastness was measured in the same manner as in Example 1. Shown in Table 1.

Example 3 A polyester cloth was dyed using the dyes shown in Table 1 according to the method of Example 1 to obtain dyed cloth having the colors shown in the table.

Wet fastness after polyurethane processing of the obtained dyed fabric (
The results are shown in Table 2.

EXAMPLE A polyester cloth was dyed using the dyes shown in Table 3 according to the method of Example 1, and a dyed cloth with the color tone shown in the table was obtained.

The wet fastness of the obtained dyed fabric after polyurethane processing was measured, and all results were good.

(Effects of the invention) The dye of the present invention has a vivid color tone and high light fastness and sublimation fastness, and the wet fastness of washing fastness, alkali sweat fastness, and water fastness decreases due to post-processing such as polyurethane processing. It is possible to maintain excellent wet fastness.

In addition, the temperature dependence and pH dependence during dyeing are excellent, and the dyes of the present invention are excellent in terms of physical dyeing properties, so it can be said that the dye of the present invention is a well-balanced and comprehensively excellent dye. can.

Although known dyes are known that are structurally quite similar to those of the present invention, all of these known dyes have significantly poorer wet fastness after further processing.

Applicant: Mitsubishi Chemical Industries, Ltd. Agent: Patent Attorney Hase - (1 other person)

Claims (1)

[Claims] (1) The following general formula [I] ▲There are mathematical formulas, chemical formulas, tables, etc.▼...[I] (In the formula, X is a halogen atom, a C_1 to C_8 alkoxy group, a trifluoromethyl group, a C_1 to C_8 alkylsulfonyl group , a formyl group, a C_1-C_8 alkylcarbonyl group, a C_1-C_8 alkoxycarbonyl group, an aryloxyalkoxycarbonyl group, or an aralkyloxycarbonyl group, and Y is a hydrogen atom, a chlorine atom, a methyl group, a C_1-C_8 alkoxy group, or an acylamino group. represents a group, R^1 is a hydrogen atom, an alkenyl group,
Aryl group, C_1-C_8 alkyl group, or C_1
~C_8 alkoxy group, cyano group, chlorine atom, acyloxy group, C_1 to C_8 alkoxyalkyl group, phenyl group, phenyloxy group, aralkyloxy group, carbamoyl group, N-alkyl-aminocarbonyl group, C_1
~C_8 alkoxycarbonyl group, phenoxyalkoxycarbonyl group, aralkyloxycarbonyl group, C_8
1 to C_8 C_1 to which may be substituted with an alkoxycarbonyloxy group, a benzyloxycarbonyloxy group, a phenyloxycarbonyloxy group, a succinimide group, a phthalic acid imide group, or a cyanoalkoxy group
A monoazo dye represented by C_8 (representing an alkyl group).